Thanks for the advice everyone. Rose, I think you have hit the nail on the head about what makes me so uncomfortable. Although I think he is needy with everyone, not just me.
My first fear is that I don't have many friends and am especially not good at cultivating long-term friendships, but this is someone I have known for 7 years now. I always thought he was a little creepy, but he's also pretty intelligent and interesting. And he's really been there for me and my family to drive us to the airport or lend a hand when things are going badly. He's also done some handyman work for us, on and off, since he's often unemployed. I really do enjoy his company sometimes, but other times (like when he wants to discuss his porn collection with me... and yes I have told him it makes me uncomfortable... many many times) he drives me bonkers. So I don't want to lose him as a resource, but maybe I have to let go of one friendship in order to let in something better and more healthy.
My second fear is that he will take it really hard if I try to break ties and he also has a bit of a vindictive streak and I'm afraid he might retaliate.
Maybe I can just put some distance in the relationship for a while instead of trying to sever completely. Maybe this is an opportunity to learn some strategies for gracefully changing the subject when he brings up things I don't want to talk about. Maybe I need to figure out what qualities in me he is mirroring back to me so I can change them and stop attracting them.
Yesterday I was in the lurch because my sitter bailed (I had to go into work for a meeting... but DH was telecommuting from home and could have conceivably covered it) and he took the kids on an outing for about 4 hours. But then he had to hang around for 3 hours and talk (with both of us) about his porn collection. After he left, we were left looking at each other like "was that worth it?"
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